We are fairly new to this situation after many years of low income and long hours but making plans to work with a qualified CPA (and maybe a CFP) is on the to do list in the near future. We live in rural WY so that limits our options quite a bit and we may need to go for something virtual/remote to find what we need.
I have never met my current CPA, we do everything remote...so thats not a factor. Just having a CPA do your taxes is worthless....but having them run the "What If" scenarios is solid gold.
Some of those good scenarios have been previously mentioned here by the many savvy dudes on Rokslide.....but when you do start making some serious dough, it gets more complicated and Tax managing things can have a huge effect long term.
Your state of WY has one of the lowest tax burdens in the US with no state income tax- so you are ahead of the game there. If you were in CA like Myself, you would be paying an additional 11-13% MINIMUM right off the top....so tax deductions are more important here.
You also have low property taxes in WY, so owning rental property is a slightly better tax advantaged investment.
General info on Side businesses; These are factored before the AMT tax schedules...where other deductions like Mortgage interest is fair game for the AMT. I think it kicks in for married folks making about $90k, not much these days. The AMT effectively limits the amount of deductions one can take. Make enough $$ and you can't write off the mortgage interest on your house. Thats simplified, It get complicated.
The key to evaluating a side business or any investment really is knowing your Effective income tax rate- what you are paying now. Businesses can take eligible expenses- that you currently pay for after tax- and move them to before tax. So let's say it's gas, home office, insurance, etc amounting to $10,000/year. $10,000 x 30%[your effective tax rate in this example] = $3000 a year you make with the business vs no business. Thats $30,000 in 10 years and if that invested it will probably be $60,000 to $100,000 in ten years, $500,000 in 20 years. Not exactly chump change.